US3976697A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Preparation of tertiary amines
Assignee: Texaco Inc
•
Filing: 1974-10-29
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Granted: 1976-08-24
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Expires: 1994-10-29
Abstract
Abstract Reductive amination of C 10 -C 26 dialkyl internal ketones, with secondary amines, using a supported nickel catalyst, results in the production of tertiary amines in excellent yield.
Inventors
- 👤 Lawrence F. Kuntschik
- 👤 Orville W. Rigdon
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 00:19
CPC Classifications
C; C07; C07C; C07C209/00; C07C209/24; C07C209/26
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
123 words
A process for the manufacture of tertiary amines of the formula ##EQU1## which each of R 1 and R 2 is alkyl of from 2 to 24 carbon atoms and the sum of the carbon atoms in R 1 and R 2 is from 10 to 26, and each of R 3 and R 4 is alkyl of from 1 to 10 carbon atoms or cycloalkyl of from 3 to 10 carbon atoms, which process consists essentially of reacting a ketone of the formula ##EQU2## with a secondary amine of the formula ##EQU3## and hydrogen in the presence of a supported nickel catalyst at a pressure of from about 100 to 2000 p.s.i.g. and a temperature of from about 100° to about 300°F.
Claim 2
Dependent Claim
123 words
A process for the manufacture of tertiary amines of the formula ##EQU1## which each of R 1 and R 2 is alkyl of from 2 to 24 carbon atoms and the sum of the carbon atoms in R 1 and R 2 is from 10 to 26, and each of R 3 and R 4 is alkyl of from 1 to 10 carbon atoms or cycloalkyl of from 3 to 10 carbon atoms, which process consists essentially of reacting a ketone of the formula ##EQU2## with a secondary amine of the formula ##EQU3## and hydrogen in the presence of a supported nickel catalyst at a pressure of from about 100 to 2000 p.s.i.g. and a temperature of from about 100° to about 300°F.
Claim 3
Dependent Claim
42 words
A process according to claim 1 in which each of R 1 and R 2 is alkyl of from 2 to 11 carbon atoms and the sum of the carbon atoms in R 1 and R 2 is from 10 to 13.
Claim 4
Dependent Claim
24 words
A process according to claim 2 in which each of R 3 and R 4 is alkyl of from 1 to 4 carbon atoms.
Claim 5
Dependent Claim
13 words
A process according to claim 3 in which the secondary amine is dimethylamine.
Claim 6
Dependent Claim
13 words
A process according to claim 3 in which the secondary amine is methyl-sec.butylamine.
Claim 7
Dependent Claim
12 words
A process according to claim 2 in which the ketone is 6-undecanone.
Claim 8
Dependent Claim
32 words
A process according to claim 2 in which the ketone is a mixed stream comprising ketones in which each of R 1 and R 2 has from 2 to 11 carbon atoms.
Claim 9
Dependent Claim
25 words
A process according to claim 1 in which the sum of the carbon atoms in R 1 and R 2 is from 13 to 26.
Claim 10
Dependent Claim
23 words
A process according claim 8 in which each of R 3 and R 4 is alkyl of from 1 to 4 carbon atoms.
Claim 11
Dependent Claim
13 words
A process according to claim 9 in which the secondary amine is dimethylamine.
Claim 12
Dependent Claim
12 words
A process according to claim 8 in which the ketone is caprylone.
Claim 13
Dependent Claim
32 words
A process according to claim 8 in which the ketone is a mixed stream comprising ketones in which each of R 1 and R 2 has from 2 to 24 carbon atoms.
Claim 14
Dependent Claim
57 words
A process according to claim 1 in which each of R 3 and R 4 is alkyl of from 1 to 4 carbon atoms, and said secondary amine is dissolved in a solvent selected from the group consisting of C 1 -C 6 alkanes, C 4 -C 8 cycloalkanes, C 1 -C 6 alcohols, tetrahydrofuran and dioxane.
Claim 15
Dependent Claim
17 words
A process according to claim 13 in which the solvent is a C 1 -C 6 alcohol.
Claim 16
Dependent Claim
12 words
A process according to claim 14 in which the solvent is methanol.
Claim 17
Dependent Claim
12 words
A process according to claim 13 in which the solvent is tetrahydrofuran.
Claim 18
Dependent Claim
12 words
A process according to claim 13 in which the solvent is dioxane.
Claim 19
Dependent Claim
52 words
A process according to claim 1 in which the catalyst is a zirconium-modified nickel catalyst in which the zirconium-modified nickel constitutes from about 0.1 to about 60 wt. % of the catalyst and the zirconium is present in an amount ranging from about 2 to about 10 wt. % of the nickel.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-08-24 | 1980-02-23 | 1980-08-24 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-08-24 | 1984-02-23 | 1984-08-24 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-08-24 | 1988-02-23 | 1988-08-24 | $7700.00 | Window Closed / Lapsed |